N-oxy- and thioalkylcarbonyloxyalkylpyrrole insecticidal, acaricidal and molluscicidal agents

ABSTRACT

There are provided N-oxy- and thioalkylcarbonyloxyalkylpyrrole compounds of formula I  and their use for the control of insects, acarina and mollusks. Further provided are compositions and methods comprising those compounds for the protection of plants from attack by insects, acarina and mollusks.

BACKGROUND OF THE INVENTION

Insects, acarina and mollusks destroy growing and harvested crops. Inthe United States alone, agronomic crops must compete with thousands ofinsect and acarid species. In particular, tobacco budworms, southernarmyworms and two-spotted spider mites and slugs are especiallydevestating to crops.

Tobacco budworms cause tremendous economic losses in agronomic crops. Inparticular, budworms devastate cotton crops by feeding on green bolls.Control of budworms is complicated by their resistance to many commoninsecticides, including organophosphates, carbamates and pyrethroids.Also, budworm larvae are difficult to control with currently availableinsecticides once they reach the third instar.

Two-spotted spider mites attack many plant species, raspberry plants forexample, by removing sap from leaves. When raspberry plants are heavilyinfested, canes and leaves become stunted. With a severe infestation,fruiting canes are damaged, resulting in reduced yield and fruitquality.

In spite of the commercial insecticides, acaricides and molluscicidesavailable today, damage to crops, both growing and harvested, caused byinsects, acarina and mollusks still occurs. Accordingly, there isongoing research to create new and more effective insecticides,acaricides and molluscicides.

Certain pyrrole compounds are known to possess insecticidal, acaricidaland/or molluscicidal activity (see, e.g., U.S. Pat. No. 5,157,047 andU.S. patent application Ser. Nos. 392 filed on Aug. 11, 1989; 621,162filed on Nov. 30, 1990; 776,967 filed on Oct. 15, 1991; 795,407 filed onNov. 20, 1991; 803,289 filed on Dec. 4, 1991; and 971,025 filed on Nov.3, 1992). However, none of the pyrroles disclosed in those patentapplications are within the scope of the present invention.

It is therefore an object of the present invention to provide N-oxy- andthioalkylcarbonyloxyalkylpyrrole compounds which are highly effectivefor controlling insects, acarina and mollusks.

It is also an object of the present invention to provide a method forprotecting growing plants from attack by insects, acarina and mollusksby applying to the foliage of said plants or to the soil or water inwhich they are growing an insecticidally, acaricidally ormolluscicidally effective amount of and N-oxy- orthioalkylcarbonyloxyalkylpyrrole compound.

These and other objects of the present invention will become moreapparent from the detailed description thereof set forth below.

SUMMARY OF THE INVENTION

The present invention describes N-oxy- andthioalkylcarbonyloxyalkylpyrrole compounds which are useful asinsecticidal, acaricidal and molluscicidal agents for the control ofinsects, acarina and mollusks and for the protection of plants fromattack by insects, acarina and mollusks.

The N-oxy- and thioalkylcarbonyloxyalkylpyrrole compounds of the presentinvention have the following structural formula I: ##STR1## wherein W isCN, NO₂, S(O)_(m) CF₂ R₄ or ##STR2## R₄ is hydrogen, F, Cl, Br, CF₂ H,CCl₂ H, CClFH, CF₃ or CCl₃ ;

m is an integer of 0, 1 or 2;

R₅ and R₆ are each independently hydrogen,

C₁ -C₄ alkyl optionally substituted with one or more halogen atoms, or

phenyl optionally substituted with one or more

halogen atoms,

NO₂ groups,

CN groups,

C₁ -C₄ alkyl groups optionally substituted with one or more halogenatoms, or

C₁ -C₄ alkoxy groups optionally substituted with one or more halogenatoms;

X is halogen, CF₃, CN, NO₂, S(O)_(m) CF₂ R₄ or

phenyl optionally substituted with one or more

halogen atoms,

NO₂ groups,

CN groups,

C₁ -C₄ alkyl groups optionally substituted with one or more halogenatoms, or

C₁ -C₄ alkoxy groups optionally substituted with one or more halogenatoms;

Y is halogen, CF₃ or

phenyl optionally substituted with one or more

halogen atoms,

NO₂ groups,

CN groups,

C₁ -C₄ alkyl groups optionally substituted with one or more halogenatoms, or

C₁ -C₄ alkoxy groups optionally substituted with one or more halogenatoms;

Z is hydrogen, halogen or CF₃ ;

R is hydrogen or C₁ -C₄ alkyl;

R₁ and R₂ are each independently hydrogen,

C₁ -C₆ alkyl optionally substituted with one or more halogen atoms,

C₁ -C₆ alkoxy optionally substituted with one or more halogen atoms,

C₁ -C₆ alkylthio optionally substituted with one or more halogen atoms,or

phenyl optionally substituted with one or more

halogen atoms,

NO₂ groups,

CN groups,

C₁ -C₄ alkyl groups optionally substituted with one or more halogenatoms, or

C₁ -C₄ alkoxy groups optionally substituted with one or more halogenatoms, or

when R₁ and R₂ are taken together with the atom to which they areattached may form a C₃ -C₆ cycloalkyl group optionally substituted withone to three C₁ -C₄ alkyl groups, C₂ -C₆ alkenyl groups or phenylgroups, or R₁ or R₂ may be taken together with R₃ and the atoms to whichthey are attached to form a 4- to 7-membered heterocyclic ring;

Q is AR₃ or ##STR3## A is O or S(O)_(p) ; p is an integer of 0,1 or 2;

R₃ is hydrogen,

C₁ -C₆ alkyl,

C₁ -C₆ alkenyl,

C₁ -C₆ alkynyl,

phenyl optionally substituted with one or more

halogen atoms,

NO₂ groups,

CN groups,

C₁ -C₄ alkyl groups optionally substituted with one or more halogenatoms, or

C₁ -C₄ alkoxy groups optionally substituted with one or more halogenatoms;

C(O)R₇ provided p is 0,

C(O)A₁ provided p is 0,

(CH₂ CH₂ O)_(n) R₇, or ##STR4## or R₃ may be taken together with eitherR₁ or R₂ and the atoms to which they are attached to form a 4-to7-membered heterocyclic ring;

Z₁ is O or S;

R₇ is

C₁ -C₆ alkyl,

C₂ -C₆ alkenyl,

C₂ -C₆ alkynyl, or

phenyl optionally substituted with one or more

halogen atoms,

NO₂ groups,

CN groups,

C₁ -C₄ alkyl groups optionally substituted with one or more halogenatoms, or

C₁ -C₄ alkoxy groups optionally substituted with one or more halogenatoms;

n is an integer of 1, 2 or 3;

R₈ and R₉ are each independently hydrogen or C₁ -C₄ alkyl, or

when taken together may form a ring wherein R₈ R₉ is represented by--CH═CH--CH═CH--;

A₁ is OR₁₀ or NR₁₁ R₁₂ ;

R₁₀ is C₁ -C₆ alkyl or

phenyl optionally substituted with one or more

halogen atoms,

NO₂ groups,

CN groups,

C₁ -C₄ alkyl groups optionally substituted with one or more halogenatoms, or

C₁ -C₄ alkoxy groups optionally substituted with one or more halogenatoms;

R₁₁ and R₁₂ are each independently hydrogen or C₁ -C₄ alkyl; and

R₁₃ is C₁ -C₄ alkyl.

This invention also relates to compositions containing those compoundsand methods for using those compounds and compositions. Advantageously,it has been found that the N-oxy- and thioalkylcarbonyloxyalkylpyrrolecompounds of the present invention, and compositions containing them,are effective insecticidal, acaricidal and molluscicidal agents for thecontrol of insects, acarina and mollusks and for the protection ofplants from attack by insects, acarina and mollusks. The compounds ofthe present invention are especially useful for the control of tobaccobudworms.

DETAILED DESCRIPTION OF THE INVENTION

Insects, acarina and mollusks destroy growing and harvested crops. Inthe United States alone, agronomic crops must compete with thousands ofinsect and acarid species. Accordingly, there is ongoing research tocreate new and more effective insecticides, acaricides and molluscicidesfor the control of insects, acarina and mollusks and for the protectionof plants from attack by insects, acarina and mollusks. There is alsoongoing research to create new insecticides and acaricides to overcomethe resistance observed with several classes of insecticidal andacaricidal agents.

Advantageously, the present invention provides a method for controllinginsects, acarina and mollusks by contacting said insects, acarina andmollusks, their breeding grounds, food supply or habitat with aninsecticidally, acaricidally or molluscicidally effective amount of aformula I, N-oxy-or thioalkylcarbonyloxyalkylpyrrole compound.

The present invention also provides a method for protecting growingplants from attack by insects, acarina and mollusks by applying to thefoliage of said plants of to the soil or water in which they are growingan insecticidally, acaricidally or molluscicidally effective amount of aformula I, N-oxy- or thioalkylcarbonyloxyalkylpyrrole compound.

The N-oxy- and thioalkylcarbonyloxyalkylpyrrole compounds of the presentinvention have the following structural formula I: ##STR5## wherein W isCN, NO₂, S(O)_(m) CF₂ R₄ or ##STR6## R₄ is hydrogen, F, Cl, Br, CF₂ H,CCl₂ H, CClFH, CF₃ or CCl₃ ;

m is an integer of 0, 1 or 2;

R₅ and R₆ are each independently hydrogen,

C₁ -C₄ alkyl optionally substituted with one or more halogen atoms, or

phenyl optionally substituted with one or more

halogen atoms,

NO₂ groups,

CN groups,

C₁ -C₄ alkyl groups optionally substituted with one or more halogenatoms, or

C₁ -C₄ alkoxy groups optionally substituted with one or more halogenatoms;

X is halogen, CF₃, CN, NO₂, S(O)_(m) CF₂ R₄ or

phenyl optionally substituted with one or more

halogen atoms,

NO₂ groups,

CN groups,

C₁ -C₄ alkyl groups optionally substituted with one or more halogenatoms, or

C₁ -C₄ alkoxy groups optionally substituted with one or more halogenatoms;

Y is halogen, CF₃ or

phenyl optionally substituted with one or more

halogen atoms,

NO₂ groups,

CN groups,

C₁ -C₄ alkyl groups optionally substituted with one or more halogenatoms, or

C₁ -C₄ alkoxy groups optionally substituted with one or more halogenatoms;

Z is hydrogen, halogen or CF₃ ;

R is hydrogen or C₁ -C₄ alkyl;

R₁ and R₂ are each independently hydrogen,

C₁ -C₆ alkyl optionally substituted with one or more halogen atoms,

C₁ -C₆ alkoxy optionally substituted with one or more halogen atoms,

C₁ -C₆ alkylthio optionally substituted with one or more halogen atoms,or

phenyl optionally substituted with one or

more halogen atoms,

NO₂ groups,

CN groups,

C₁ -C₄ alkyl groups optionally substituted with one or more halogenatoms, or

C₁ -C₄ alkoxy groups optionally substituted with one or more halogenatoms, or

when R₁ and R₂ are taken together with the atom to which they areattached may form a C₃ -C₆ cycloalkyl group optionally substituted withone to three C₁ -C₄ alkyl groups, C₂ -C₆ alkenyl groups or phenylgroups, or R₁ or R₂ may be taken together with R₃ and the atoms to whichthey are attached to form a 4- to 7-membered heterocyclic ring;

Q is AR₃ or ##STR7## A is O or S(O)_(p) ; p is an integer of 0,1 or 2;

R₃ is hydrogen,

C₁ -C₆ alkyl,

C₁ -C₆ alkenyl,

C₁ -C₆ alkynyl,

phenyl optionally substituted with one or more

halogen atoms,

NO₂ groups,

CN groups,

C₁ -C₄ alkyl groups optionally substituted with one or more halogenatoms, or

C₁ -C₄ alkoxy groups optionally substituted with one or more halogenatoms,

C(O)R₇ provided p is 0,

C(O)A₁ provided p is 0,

(CH₂ CH₂ O)_(n) R₇, or ##STR8## or R₃ may be taken together with eitherR₁ or R₂ and the atoms to which they are attached to form a 4- to7-membered heterocyclic ring;

Z₁ is O or S;

R₇ is

C₁ -C₆ alkyl,

C₂ -C₆ alkenyl,

C₂ -C₆ alkynyl, or

phenyl optionally substituted with one or more

halogen atoms,

NO₂ groups,

CN groups,

C₁ -C₄ alkyl groups optionally substituted with one or more halogenatoms, or

C₁ -C₄ alkoxy groups optionally substituted with one or more halogenatoms;

n is an integer of 1, 2 or 3;

R₈ and R₉ are each independently hydrogen or C₁ -C₄ alkyl, or

when taken together may form a ring wherein

R₈ R₉ is represented by --CH═CH--CH═CH--;

A₁ is OR₁₀ or NR₁₁ R₁₂ ;

R₁₀ is C₁ -C₆ alkyl or

phenyl optionally substituted with one or more

halogen atoms,

NO₂ groups,

CN groups,

C₁ -C₄ alkyl groups optionally substituted with one or more halogenatoms, or

C₁ -C₄ alkoxy groups optionally substituted with one or more halogenatoms;

R₁₁ and R₁₂ are each independently hydrogen or C₁ -C₄ alkyl; and

R₁₃ is C₁ -C₄ alkyl.

Preferred formula I compounds of the invention are those wherein

W is CN, NO₂, S(O)_(m) CF₂ R₄ or ##STR9## R₄ is hydrogen, F, Cl, Br, CF₂H, CCl₂ H, CClFH, CF₃ or CCl₃ ;

m is an integer of 0, 1 or 2;

R₅ and R₆ are each independently hydrogen or C₁ -C₄ alkyl;

X is Cl, Br, CF₃ or

phenyl optionally substituted with one or more

halogen atoms,

NO₂ groups,

CN groups,

C₁ -C₄ alkyl groups optionally substituted with one or more halogenatoms, or

C₁ -C₄ alkoxy groups optionally substituted with one or more halogenatoms;

Y is Cl, Br, CF₃ or

phenyl optionally substituted with one or more

halogen atoms,

NO₂ groups,

CN groups,

C₁ -C₄ alkyl groups optionally substituted with one or more halogenatoms, or

C₁ -C₄ alkoxy groups optionally substituted with one or more halogenatoms;

Z is Cl, Br or CF₃ ;

R is hydrogen;

R₁ and R₂ are each independently hydrogen,

C₁ -C₆ alkyl optionally substituted with one or more halogen atoms, or

R₁ or R₂ may be taken together with R₃ and the atoms to which they areattached to form a 5- to 6-membered heterocyclic ring;

Q is AR₃ or ##STR10## A is O or S; R₃ is C₁ -C₆ alkyl,

phenyl optionally substituted with one or more

halogen atoms,

NO₂ groups,

CN groups,

C₁ -C₄ alkyl groups optionally substituted with one or more halogenatoms, or

C₁ -C₄ alkoxy groups optionally substituted with one or more halogenatoms,

(CH₂ CH₂ O)_(n) R₇, or ##STR11## or R₃ may be taken together with eitherR₁ or R₂ and the atoms to which they are attached to form a 5-to6-membered heterocyclic ring;

Z₁ is O or S;

R₇ is C₁ -C₆ alkyl,

n is an integer of 1, 2 or 3;

R₈ and R₉ are each independently hydrogen or C₁ -C₄ alkyl, or

when taken together may form a ring wherein R₈ R₉ is represented by--CH═CH--CH═CH--; and

R₁₃ is C₁ -C₄ alkyl.

More preferred insecticidal, acaricidal and molluscicidal compounds ofthis invention are those wherein

W is CN;

X is phenyl optionally substituted with one or more

halogen atoms,

NO₂ groups,

CN groups,

C₁ -C₄ alkyl groups optionally substituted with one or more halogenatoms, or

C₁ -C₄ alkoxy groups optionally substituted with one or more halogenatoms;

Y is Cl or Br;

Z is Cl, Br or CF₃ ;

R is hydrogen;

R₁ and R₂ are each independently hydrogen or

C₁ -C₆ alkyl, or

R₁ or R₂ may be taken together with R₃ and

the atoms to which they are attached to form

a 5- to 6-membered heterocyclic ring;

Q is AR₃ or ##STR12## A is O or S; R₃ is C₁ -C₆ alkyl,

phenyl optionally substituted with one or more

halogen atoms,

NO₂ groups,

CN groups,

C₁ -C₄ alkyl groups optionally substituted with one or more halogenatoms, or

C₁ -C₄ alkoxy groups optionally substituted with one or more halogenatoms,

(CH₂ CH₂ O)_(n) R₇, or ##STR13## or R₃ may be taken together with eitherR₁ or R₂ and the atoms to which they are attached to form a 5-memberedheterocyclic ring;

Z₁ is O or S;

R₇ is C₁ -C₆ alkyl,

n is an integer of 1, 2 or 3; and

R₁₃ is C₁ -C₄ alkyl.

Most preferred compounds of this invention which are especiallyeffective insecticidal, acaricidal and molluscicidal agents are thosehaving the structural formula II: ##STR14## wherein W is CN;

X is phenyl optionally substituted with one or more

halogen atoms,

NO₂ groups,

CN groups,

C₁ -C₄ alkyl groups optionally substituted with one or more halogenatoms, or

C₁ -C₄ alkoxy groups optionally substituted with one or more halogenatoms;

Y is Cl or Br;

Z is Cl, Br or CF₃ ;

R is hydrogen;

R₁ and R₂ are each independently hydrogen or

C₁ -C₆ alkyl, or

R₁ or R₂ may be taken together with R₃ and the atoms to which they areattached to form a 5-membered heterocyclic ring;

Q is AR₃ or ##STR15## A is O or S; R₃ is C₁ -C₆ alkyl,

phenyl optionally substituted with one or more

halogen atoms,

NO₂ groups,

CN groups,

C₁ -C₄ alkyl groups optionally substituted with one or more halogenatoms, or

C₁ -C₄ alkoxy groups optionally substituted with one or more halogenatoms;

(CH₂ CH₂ O)_(n) R₇, or ##STR16## or R₃ may be taken together with eitherR₁ or R₂ and the atoms to which they are attached to form a 5-memberedheterocyclic ring;

Z₁ is O or S;

R₇ is C₁ -C₆ alkyl,

n is an integer of 1, 2 or 3; and

R₁₃ is C₁ -C₄ alkyl.

Exemplary of halogen hereinabove are fluorine, chlorine, bromine andiodine.

Advantageously, it has been found that the formula I compounds of thepresent invention are especially useful for the control of tobaccobudworms, southern armyworms and two-spotted spider mites.

Formula I compounds may be prepared as shown in Flow Diagram I.##STR17## wherein R₁₄ is C₁ -C₆ alkyl optionally substituted with one tothree halogen atoms,

phenyl optionally substituted with one or two halogen, CN, NO₂, C₁ -C₄alkyl, C₁ -C₄ alkoxy or CF₃ groups,

2- or 3-thienyl or

2- or 3-furyl;

X₁ is Cl or Br; and

W, X, Y, Z, R, R₁, R₂ and Q are as described hereinabove for formula I.

The appropriately substituted pyrrole of formula III is reacted with analkylating agent of formula IV in the presence of an alkali metalhydride or an alkali metal C₁ -C₆ alkoxide to form anN-alkanoylaminomethyl or N-aroylaminomethylpyrrole of formula V, saidformula V aminomethylpyrrole is then reacted with an excess ofphosphorous oxychloride or phosphorus oxybromide to form a1-halomethylpyrrole of formula VI. Said 1-halomethylpyrrole is reactedwith a carboxylic acid of formula VII in the presence of an alkali metalhydroxide, such as sodium or potassium hydroxide, to form desired N-oxy-and thioalkylcarbonyloxyalkylpyrrole compounds of formula I.

Starting formula III pyrrole compounds may be prepared according to theprocedures described in U.S. Pat. No. 5,157,047 and U.S. patentapplication Ser. Nos. 392 filed on Aug. 11, 1989; 621,162 filed on Nov.30, 1990; 776,967 filed on Oct. 15, 1991; 795,407 filed on Nov. 20,1991; 803,289 filed on Dec. 4, 1991; and 971,025 filed on Nov. 3, 1992and are incorporated herein by reference thereto. Starting formula IValkylating agents are described in U.S. patent application Ser. No.755,935 filed on Sep. 6, 1991 and is incorporated herein by referencethereto. In addition, certain formula VI 1-halomethylpyrrole compoundswherein W is CN may be prepared as described in U.S. Pat. No. 5,118,816.

The N-oxy- and thioalkylcarbonyloxyalkylpyrrole compounds of the presentinvention are effective for controlling insects, acarina and mollusks.Those compounds are also effective for protecting growing or harvestedcrops from attack by insects, acarina and mollusks.

Insects controlled by the formula I compounds of this invention includeLepidoptera such as tobacco budworms, cabbage loopers, cotton bollworms, beet armyworms, southern armyworms and diamondback moths;Homoptera such as aphids, leaf hoppers, plant hoppers and white flies;Thysanoptera such as thrips; Coleoptera such as boll weevils, Coloradopotato beetles, southern corn rootworms and mustard beetles; andOrthoptera such as locusts, crickets, grasshoppers and cockroaches.Acarina controlled by the compounds of this invention include mites suchas two-spotted spider mites, carmine spider mites, banks grass mites,strawberry mites, citrus rust mites and leprosis mites. Molluskscontrolled by the compounds of this invention include gastropoda such assnails, slugs, cowries and limpets. Advantageously, it has been foundthat the compounds of the present invention are especially effectiveagainst tobacco budworms, southern armyworms, two-spotted spider mitesand slugs.

In practice, generally about 10 ppm to 10,000 ppm and preferably about100 ppm to about 5,000 ppm of a formula I compound, dispersed in wateror another liquid carrier, is effective when applied to the plants, thecrops or the soil in which said crops are growing to protect said cropsfrom attack by insects, acarina and mollusks.

The formula I compounds of this invention are also effective forcontrolling insects, acarina and mollusks, when applied to the foliageof plants and/or to the soil or water in which said plants are growingin sufficient amount to provide a rate of from about 0.100 kg/ha to 4.0kg/ha of active ingredient.

While the compounds of this invention are effective for controllinginsects, acarina and mollusks when employed alone, they may also be usedin combination with other biological chemicals, including otherinsecticides, acaricides and molluscicides. For example, the formula Icompounds of this invention may be used effectively in conjunction orcombination with pyrethroids, phosphates, carbamates, cyclodienes,endotoxin of bacillus thuringiensis (Bt), formamidines phenol tincompounds, chlorinated hydrocarbons, benzoylphenyl ureas and the like.

The compounds of this invention may be formulated as emulsifiableconcentrates, flowable concentrates or wettable powders which arediluted with water or other suitable polar solvent, generally in situ,and then applied as a dilute spray. Said compounds may also beformulated in dry compacted granules, granular formulations, dusts, dustconcentrates, suspension concentrates, microemulsions and the like allof which lend themselves to seed, soil, water and/or foliageapplications to provide the requisite plant protection. Suchformulations include the compounds of the invention admixed with inert,solid or liquid diluents.

For example, wettable powders, dusts, and dust concentrate formulationscan be prepared by grinding and blending together about 25% to about 85%by weight of formula I compounds and about 75% to about 15% by weight ofa solid diluent such as bentonite, diatomaceous earth, kaolin,attapulgite, or the like, about 1% to 5% by weight of a dispersing agentsuch as sodium lignosulfonate, and about 1% to 5% by weight of anonionic surfactant, such as octylphenoxy polyethoxy ethanol,nonylphenoxy polyethoxy ethanol or the like.

A typical emulsifiable concentrate can be prepared by dissolving about15% to about 70% by weight of a formula I compound in about 85% to about30% by weight of a solvent such as isohporone, toluene, butylcellosolve, methyl acetate, propylene glycol monomethyl ether, or thelike and dispersing therein about 1% to 5% by weight of a nonionicsurfactant such as an alkylphenoxy polyethoxy alcohol.

An especially effective method for controlling terrestrial gastropodswith the formula I compounds of the invention, is to proffer the activemolluscicidal material in the form of a bait formulation. These baitformulations can be widely varied but generally contain about 1% to 20%by weight of the active ingredient, about 40% to 50% by weight of solidedible nutritive substance, about 5% to 10% by weight of a carbohydratesource such as sugar, molasses, corn syrup or the like and the remainderof the formulation, i.e. about 30% to 50% by weight of water or otherconsumable liquid.

In order to facilitate a further understanding of the invention, thefollowing examples are presented to illustrate more specific detailsthereof. The invention is not to be limited thereby except as defined inthe claims.

EXAMPLE 1 Preparation of[3-Bromo-5-(;-chlorophenyl)-4-cyano-2-(trifluoromethyl)pyrrol-1-yl]methyl2-phenoxypropionate ##STR18##

4-Bromo1-(bromomethyl)-2-(p-chlorophenyl)-5-(trifluormethyl)pyrrole-3-carbonitrile(2.5 g, 5.7 mmol) is added to a mixture of 2-phenoxypropionic acid (1.9g, 11.4 mmol) and sodium hydroxide (0.46 g, 11.4 mmol) inN,N-dimethylformamide. The reaction mixture is stirred for one hour at50° C. and diluted with a 3:2 ethyl acetate/water mixture. The organicphase is separated, dried over MgSO₄ and concentrated in vacuo to obtaina tan oil. The oil is crystallized from 2-propanol to give the titleproduct as a yellow solid (2.7 g, mp 101°-103° C.).

Using essentially the same procedure, but employing the appropriatelysubstituted 1-(halomethyl)pyrrole and carboxylic acid, the followingcompounds are obtained:

    __________________________________________________________________________     ##STR19##                                                                    L M  Y  Z  R.sub.1                                                                         R.sub.2                                                                          R.sub.3      A  mp °C.                                 __________________________________________________________________________    H Cl Br CF.sub.3                                                                         H H                                                                                 ##STR20##   O  117-118                                       H Cl Br CF.sub.3                                                                         H H  CH.sub.3     O  100-101                                       H Cl Br CF.sub.3                                                                         H H                                                                                 ##STR21##   S  oil                                           H Cl Br CF.sub.3                                                                         H H                                                                                 ##STR22##   O  132-134                                       H Cl Br CF.sub.3                                                                         H H                                                                                 ##STR23##   O  165.5-168                                     H Cl Br CF.sub.3                                                                         CHCHCH            S  110-111.5                                     H Cl Br CF.sub.3                                                                         CHCHCH            O  101-102                                       Cl                                                                              Cl Cl Cl H H                                                                                 ##STR24##   S  79.5-82                                       Cl                                                                              Cl Cl Cl H H                                                                                 ##STR25##   O  103.5-105                                     Cl                                                                              Cl Cl Cl H CH.sub.3                                                                          ##STR26##   O  112-115                                       H Cl Br CF.sub.3                                                                         H H  (CH.sub.2 CH.sub.2 O).sub.3 CH.sub.3                                                       O  oil                                           H CF.sub.3                                                                         Cl Cl H H                                                                                 ##STR27##   O  195-197                                       H CF.sub.3                                                                         Cl Cl CHCHCH            O  125-128                                       H Cl Br CF.sub.3                                                                         H CH.sub.2CH.sub.2CH.sub.2                                                                      O  121-123                                       H CF.sub.3                                                                         Cl Cl H CH.sub.2CH.sub.2CH.sub.2                                                                      O  104-106.5                                     H CF.sub.3                                                                         Cl Cl H CH.sub.2CH.sub.2CH.sub.2                                                                      S  84- 86.5                                      __________________________________________________________________________

EXAMPLE 2 Preparation of[3-Chloro-5-(p-chlorophenyl)-4-cyano-2-(trifluoromethyl)pyrrol-1-yl]methyl(dimethylphosphono)acetate ##STR28##

A solution of potassium (dimethylphosphono)acetate (0.69 g, 4 mmol) inN,N-dimethylformamide is treated with1-(bromomethyl)-4-chloro-2-(p-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile(0.79 g, 2 mmol), stirred at room temperature for one hour, diluted withwater and extracted with ethyl acetate. The combined organic extractsare washed sequentially with water and brine, dried over anhydrous MgSO₄and concentrated in vacuo to obtain a brown oil. The oil ischromatographed using silica gel and a 1:1 hexanes/ethyl acetate mixtureto give the title product as a viscous yellow oil (0.41 g) which isidentified by ¹³ C and ¹⁹ FNMR spectral analyses.

EXAMPLE 3 Insecticide and acaricide evaluations

The following tests show the efficacy of the compounds as insecticidesand acaricides. The evaluaitons are conducted with solutions of testcompounds dissolved or dispersed in 50/50 acetone/water mixtures. Thetest compound is technical material dissolved or dispersed in saidacetone/water mixtures in sufficient amounts to provide theconcentrations set forth in Table I below.

All concentrations reported herein are in terms of active ingredient.All tests are conducted in a laboratory maintained at about 27° C. Therating system employed is as follows:

    ______________________________________                                        Rating System                                                                 ______________________________________                                                   0 =  no effect                                                                1 =  10-25% kill                                                              2 =  26-35% kill                                                              3 =  36-45% kill                                                              4 =  46-55% kill                                                              5 =  56-65% kill                                                              6 =  66-75% kill                                                              7 =  76-85% kill                                                              8 =  86-99% kill                                                              9 =  100% kill                                                                -- = no evaluation                                                 ______________________________________                                    

The test species of insects used in the present evaluations along withspecific test procedures are described below.

Spodoptera eridania 3rd instar larvae, southern armyworm

A sieva lima bean leaf expanded to 7 to 8 cm in length is dipped in thetest suspension with agitation for 3 seconds and placed in a hood todry. The leaf is then placed in a 100×10 mm petri dish containing a dampfilter paper on the bottom and 10 3rd instar caterpillars. The dish ismaintained for 5 days before observations are made of mortality, reducedfeeding or an interference with normal moulting.

Tetranychus urticae (OP-resistant strain), 2-spotted spider mite

Sieva lima bean plants with primary leaves expanded to 7 to 8 cm areselected and cut back to one plant per pot. A small piece is cut from aleaf taken from the main colony and placed on each leaf of the testplants. This is done about 2 hours before treatment to allow the mitesto move over to the test plant and to lay eggs. The size of the cutpiece is varied to obtain about 100 mites per leaf. At the time of thetreatment, the piece of leaf used to transfer the mites is removed anddiscarded. The mite-infested plants are dipped in the test formulationfor 3 seconds with agitation and set in the hood to dry. Plants are keptfor 2 days before estimates of adult kill are made.

Empoasca abrupta, adults, western potato leafhopper

A Sieva lima bean leaf about 5 cm long is dipped in the test formulationfor 3 seconds with agitation and placed in a hood to dry. The leaf isplaced in a 100×10 mm petri dish containing a moist filter paper on thebottom. About 10 adult leafhoppers are added to each dish and thetreatments are kept for 3 days before mortality counts are made.

Heliothis virenscens, 3rd instar tobacco budworm

Cotton cotyledons are dipped in the test formulation and allowed to dryin a hood. When dry, each is cut into quarters and ten sections placedindividually in 30 mL plastic medicine cups containing a 5 to 7 mm longpiece of damp dental wick. One 3rd instar caterpillar is added to eachcup and a cardboard lid placed on the cup. Treatments are maintained for3 days before mortality counts and estimates of reduction in feedingdamage are made.

Diabrotic undecimpunctata howardi, third instar southern corn rootworm

One cc of fine talc is placed in a 30 mL wide-mouth screw-top glass jar.One mL of the appropriate acetone test solution is pipetted onto thetalc so as to provide 1.25 and 0.25 mg of active ingredient per jar. Thejars are set under a gentle air flow until the acetone is evaporated.The dried talc is loosened, 1 cc of millet seed is added to serve asfood for the insects and 25 mL of moist soil is added to each jar. Thejars are capped and the contents throroughly mixed on a Vortex Mixer.Following this, ten 3rd instar rootworms are added to each jar and thejars are loosely capped to allow air exchange for the larvae. Thetreatments are held for 6 days before mortality counts are made. Missinglarvae are presumed dead, since they decompose rapidly and can not befound. The concentrations used in this test correspond approximately to50 and 10 kg/ha, respectively.

The data obtained for the above described evaluations are reported inTable I.

                                      TABLE I                                     __________________________________________________________________________    Insecticide And Acaricide Evaluations                                                                                   Southern                                                  OP-Resistant                                                                         Leaf-                                                                              Tobacco Corn                                              Armyworm                                                                              Mites  hopper                                                                             Budworm Rootworm                                          (ppm)   (ppm)  (ppm)                                                                              (ppm)   (kg/ha)                             Compound      1000                                                                             100                                                                              10                                                                              300                                                                              100 100                                                                              10                                                                              1000                                                                             100                                                                              10                                                                              50 10                               __________________________________________________________________________    [4-Bromo-2-(p-chloro-                                                                       9  9  9 9  9   9  8.5                                                                             9  9  8.5                                                                             9  7                                phenyl)-3-cyano-5-(tri-                                                       fluoromethyl)pyrrol-1-                                                        yl]methyl phenoxyacetate                                                      [3-Bromo-5-(p-chloro-                                                                       9  9  9 9  9   9  9 9  9  9 9  6                                phenyl)-4-cyano-2-(tri-                                                       fluoromethyl)pyrrol-1-                                                        yl]methyl methyl carbonate                                                    [3-Bromo-5-(p-chloro-                                                                       9  9  9 9  9   9  9 9  9  7 4.5                                                                              0                                phenyl)-4-cyano-2-(tri-                                                       fluoromethyl)pyrrol-1-yl]-                                                    methyl (phenylthio)acetate                                                    [3-Bromo-5-(p-chloro-                                                                       9  9  9 9  9   9  4 9  9  9 9  6                                phenyl)-4-cyano-2-(tri-                                                       fluoromethyl)pyrrol-1-yl]-                                                    methyl (p-chlorophenoxy)-                                                     acetate                                                                       [3-Bromo-5-(p-chloro-                                                                       9  9  9 9  8   9  6 9  9  8.5                                                                             9  0                                phenyl)-4-cyano-2-(tri-                                                       fluoromethyl)pyrrol-1-                                                        yl]methyl 2-phenoxy-                                                          propionate                                                                    [3-Bromo-5-(p-chloro-                                                                       9  9  9 0  --  2  --                                                                              9  9  6 0  --                               phenyl)-4-cyano-2-(tri-                                                       fluoromethyl)pyrrol-1-                                                        yl]methyl 2-(benzo-                                                           thiazol-2-yloxy)acetate                                                       [3-Bromo-5-(p-chloro-                                                                       9  9  9 0  --  9  6.5                                                                             9  9  8.5                                                                             9  8                                phenyl)-4-cyano-2-(tri-                                                       fluoromethyl)pyrrol-1-                                                        yl]methyl 2-thiophene-                                                        carboxylate                                                                   [3-Bromo-5-(p-chloro-                                                                       9  9  9 9  9   9  8 9  9  8.5                                                                             8.5                                                                              9                                phenyl)-4-cyano-2-(tri-                                                       fluoromethyl)pyrrol-1-                                                        yl]methyl 2-furoate                                                           [2,3-Dichloro-4-cyano-                                                                      9  9  9 5  --  4  0 9  9  0 0  --                               5-(3,4-dichlorophenyl)-                                                       pyrrol-1-yl]methyl                                                            (phenylthio)acetate                                                           [2,3-Dichloro-5-(3,4-                                                                       9  9  9 9  0   6  0 9  9  0 0  --                               dichlorophenyl)-4-                                                            cyanopyrrol-1-yl]methyl                                                       2-phenoxyacetate                                                              [2,3-Dichloro-5-(3,4-                                                                       9  4.5                                                                              0 0  0   0  0 9  6.5                                                                              0 0  --                               dichlorophenyl)-4-cyano-                                                      pyrrol-1-yl]methyl 2-                                                         methyl-2-phenoxypropionate                                                    [3-Bromo-5-(p-chloro-                                                                       9  9  9 9  0   9  9 9  9  7.5                                                                             9  6                                phenyl)-4-cyano-2-(tri-                                                       fluoromethyl)pyrrol-1-                                                        yl]methyl {2-[2-(2-                                                           methoxyethoxy)ethoxy]-                                                        ethoxy}acetate                                                                [2,3-Dichloro-4-cyano-                                                                      9  9  0 0  --  4.7                                                                              0 9  6  0 0  --                               5-(alpha,alpha,alpha-                                                         trifluoro-p-tolyl)-                                                           pyrrol-1-yl]methyl 2-                                                         (benzothiazol-2-yl-                                                           oxy)acetate                                                                   [3,4-Dichloro-4-cyano-                                                                      9  9  9 7  9   9  0 9  9  4 5.5                                                                              0                                5-(alpha,alpha,alpha-                                                         trifluoromethyl-p-tolyl)-                                                     pyrrol-1-yl]methyl 2-                                                         furoate                                                                       [3-Bromo-5-(p-chloro-                                                                       9  9  9 9  9   9  3 9  9  6 0  --                               phenyl)-4-cyano-2-(tri-                                                       fluoromethyl)pyrrol-1-                                                        yl]methyl tetrahydro-                                                         2-furoate                                                                     [2,3-Dichloro-4-cyano-                                                                      9  9  9 0  --  9  9 9  9  3 0  --                               5-(alpha,alpha,alpha-                                                         trifluoro-p-tolyl)pyrrol-                                                     1-yl]methyl tetrahydro-                                                       2-furoate                                                                     [2,3-Dichloro-4-cyano-                                                                      9  9  9 0  --  9  3 -- 9  4 0  --                               5-(alpha,alpha,alpha-                                                         trifluoro-p-tolyl)-                                                           pyrrol-1-yl]methyl                                                            2-thiophenecarboxylate                                                        [3-Chloro-5-(p-chloro-                                                                      -- 9  9 -- 7   9  8 -- 9  9 9  9                                phenyl)-4-cyano-2-(tri-                                                       fluoromethyl)pyrrol-1-                                                        yl]methyl (dimethyl-                                                          phosphono)acetate                                                             __________________________________________________________________________

We claim:
 1. A compound having the structural formula ##STR29## whereinW is CN, NO₂, S(O)_(m) CF₂ R₄ or ##STR30## R₄ is hydrogen, F, Cl, Br,CF₂ H, CCl₂ H, CF₃ or CCl₃ ;m is an integer of 0, 1 or 2; R₅ and R₆ areeach independently hydrogen,C₁ -C₄ alkyl optionally substituted with oneor more halogen atoms, or phenyl optionally substituted with one ormorehalogen atoms, NO₂ groups, CN groups, C₁ -C₄ alkyl groups optionallysubstituted with one or more halogen atoms, or C₁ -C₄ alkoxy groupsoptionally substituted with one or more halogen atoms; X is halogen,CF₃, CN, NO₂, S(O)_(m) CF₂ R₄ orphenyl optionally substituted with oneor morehalogen atoms, NO₂ groups, CN groups, C₁ -C₄ alkyl groupsoptionally substituted with one or more halogen atoms, or C₁ -C₄ alkoxygroups optionally substituted with one or more halogen atoms; Y ishalogen, CF₃ orphenyl optionally substituted with one or morehalogenatoms, NO₂ groups, CN groups, C₁ -C₄ alkyl groups optionally substitutedwith one or more halogen atoms, or C₁ -C₄ alkoxy groups optionallysubstituted with one or more halogen atoms; Z is hydrogen, halogen orCF₃ ; R is hydrogen or C₁ -C₄ alkyl; R₁ and R₂ are each independentlyhydrogen,C₁ -C₆ alkyl optionally substituted with one or more halogenatoms, C₁ -C₆ alkoxy optionally substituted with one or more halogenatoms, C₁ -C₆ alkylthio optionally substituted with one or more halogenatoms, or phenyl optionally substituted with one or morehalogen atoms,NO₂ groups, CN groups, C₁ -C₄ alkyl groups optionally substituted withone or more halogen atoms, or C₁ -C₄ alkoxy groups optionallysubstituted with one or more halogen atoms, or when R₁ and R₂ are takentogether with the atom to which they are attached may form a C₃ -C₆cycloalkyl group optionally substituted with one to three C₁ -C₄ alkylgroups, C₂ -C₆ alkenyl groups or phenyl groups, or R₁ or R₂ may be takentogether with R₃ and the atoms to which they are attached to form a 4-to 7-membered heterocyclic ring; Q is AR₃ or ##STR31## A is O orS(O)_(p) ; p is an integer of 0, 1 or 2; R₃ is hydrogen,C₁ -C₆ alkyl, C₂-C₆ alkenyl, C₂ -C₆ alkynyl, phenyl optionally substituted with one ormorehalogen atoms, NO₂ groups, CN groups, C₁ -C₄ alkyl groups optionallysubstituted with one or more halogen atoms, or C₁ -C₄ alkoxy groupsoptionally substituted with one or more halogen atoms, C(O)R₇ provided pis 0, C(O)A₁ provided p is 0, (CH₂ CH₂ O)_(n) R₇, or ##STR32## or R₃ maybe taken together with either R₁ or R₂ and the atoms to which they areattached to form a 4- to 7-membered heterocyclic ring; Z₁ is O or S; R₇isC₁ -C₆ alkyl, C₂ -C₆ alkenyl, C₂ -C₆ alkynyl, or phenyl optionallysubstituted with one or morehalogen atoms, NO₂ groups, CN groups, C₁ -C₄alkyl groups optionally substituted with one or more halogen atoms, orC₁ -C₄ alkoxy groups optionally substituted with one or more halogenatoms; n is an integer of 1, 2 or 3; R₈ and R₉ are each independentlyhydrogen or C₁ -C₄ alkyl, orwhen taken together may form a ring whereinR₈ R₉ is represented by --CH═CH--CH═CH--; A₁ is OR₁₀ or NR₁₁ R₁₂ ; R₁₀is C₁ -C₆ alkyl orphenyl optionally substituted with one ormore halogenatoms, NO₂ groups, CN groups, C₁ -C₄ alkyl groups optionally substitutedwith one or more halogen atoms, or C₁ -C₄ alkoxy groups optionallysubstituted with one or more halogen atoms; R₁₁ and R₁₂ are eachindependently hydrogen or C₁ -C₄ alkyl; and R₁₃ is C₁ -C₄ alkyl.
 2. Thecompound according to claim 1 whereinW is CN, NO₂, S(O)_(m) CF₂ R₄ or##STR33## R₄ is hydrogen, F, Cl, Br, CF₂ H, CCl₂ H, CF₃ or CCl₃ ; m isan integer of 0, 1 or 2; R₅ and R₆ are each independently hydrogen or C₁-C₄ alkyl; X is Cl, Br, CF₃ orphenyl optionally substituted with one ormorehalogen atoms, NO₂ groups, CN groups, C₁ -C₄ alkyl groups optionallysubstituted with one or more halogen atoms, or C₁ -C₄ alkoxy groupsoptionally substituted with one or more halogen atoms; Y is Cl, Br, CF₃orphenyl optionally substituted with one or morehalogen atoms, NO₂groups, CN groups, C₁ -C₄ alkyl groups optionally substituted with oneor more halogen atoms, or C₁ -C₄ alkoxy groups optionally substitutedwith one or more halogen atoms; Z is Cl, Br or CF₃ ; R is hydrogen; R₁and R₂ are each independently hydrogen,C₁ -C₆ alkyl optionallysubstituted with one or more halogen atoms, or R₁ or R₂ are takentogether with R₃ and the atoms to which they are attached to form a 5-to 6-membered heterocyclic ring; Q is AR₃ or ##STR34## A is O or S; R₃is C₁ -C₆ alkyl,phenyl optionally substituted with one or morehalogenatoms, NO₂ groups, CN groups, C₁ -C₄ alkyl groups optionally substitutedwith one or more halogen atoms, or C₁ -C₄ alkoxy groups optionallysubstituted with one or more halogen atoms; (CH₂ CH₂ O)_(n) R₇, or##STR35## or R₃ may be taken together with either R₁ or R₂ and the atomsto which they are attached to form a 5- to 6-membered heterocyclic ring;Z₁ is O or S; R₇ is C₁ -C₆ alkyl, n is an integer of 1, 2 or 3; R₈ andR₉ are each independently hydrogen or C₁ -C₄ alkyl, orwhen takentogether may form a ring wherein R₈ R₉ is represented by--CH═CH--CH═CH--; and R₁₃ is C₁ -C₄ alkyl.
 3. The compound according toclaim 2 wherein W is CN;X is phenyl optionally substituted with one ormorehalogen atoms, NO₂ groups, CN groups, C₁ -C₄ alkyl groups optionallysubstituted with one or more halogen atoms, or C₁ -C₄ alkoxy groupsoptionally substituted with one or more halogen atoms; Y is Cl or Br; Zis Cl, Br or CF₃ ; R is hydrogen; R₁ and R₂ are each independentlyhydrogen orC₁ -C₆ alkyl, or R₁ or R₂ are taken together with R₃ and theatoms to which they are attached to form a 5-membered heterocyclic ring;Q is AR₃ or ##STR36## A is O or S; R₃ is C₁ -C₆ alkyl,phenyl optionallysubstituted with one or morehalogen atoms, NO₂ groups, CN groups, C₁ -C₄alkyl groups optionally substituted with one or more halogen atoms, orC₁ -C₄ alkoxy groups optionally substituted with one or more halogenatoms, (CH₂ CH₂ O)_(n) R₇, or ##STR37## or R₃ may be taken together witheither R₁ or R₂ and the atoms to which they are attached to form a5-membered heterocyclic ring; Z₁ is O or S; R₇ is C₁ -C₆ alkyl, n is aninteger of 1, 2 or 3; and R₁₃ is C₁ -C₄ alkyl.
 4. The compound accordingto claim 3 wherein the compound has the structural formula ##STR38## 5.The compound according to claim 4[3-bromo-5-(p-chlorophenyl)-4-cyano-2-(trifluoromethyl)pyrrol-1-yl]methylmethyl carbonate.
 6. The compound according to claim 4[3-bromo-5-(p-chlorophenyl)-4-cyano-2-(trifluoromethyl)pyrrol-1-yl]methyl2-furoate.
 7. The compound according to claim 4[4-bromo-2-(p-chlorophenyl)-3-cyano-5-(trifluoromethyl)pyrrol-1-yl]methylphenoxyacetate.
 8. The compound according to claim 4[3-bromo-5-(p-chlorophenyl)-4-cyano-2-(trifluoromethyl)pyrrol-1-yl]methyl(p-chlorophenoxy)acetate.
 9. The compound according to claim 4[3-bromo-5-(p-chlorophenyl)-4-cyano-2-(trifluoromethyl)pyrrol-1-yl]methyl(phenylthio)acetate.
 10. A method for controlling insects, acarina andmollusks which comprises contacting said insects, acarina and mollusks,their breeding ground, food supply or habitat with an insecticidally,acaricidally or molluscicidally effective amount of a compound havingthe structural formula ##STR39## wherein W is CN, NO₂, S(O)_(m) CF₂ R₄or ##STR40## R₄ is hydrogen, F, Cl, Br, CF₂ H, CCl₂ H, CF₃ or CCl₃ ;m isan integer of 0, 1 or 2; R₅ and R₆ are each independently hydrogen,C₁-C₄ alkyl optionally substituted with one or more halogen atoms, orphenyl optionally substituted with one or morehalogen atoms, NO₂ groups,CN groups, C₁ -C₄ alkyl groups optionally substituted with one or morehalogen atoms, or C₁ -C₄ alkoxy groups optionally substituted with oneor more halogen atoms; X is halogen, CF₃, CN, NO₂, S(O)_(m) CF₂ R₄orphenyl optionally substituted with one or morehalogen atoms, NO₂groups, CN groups, C₁ -C₄ alkyl groups optionally substituted with oneor more halogen atoms, or C₁ -C₄ alkoxy groups optionally substitutedwith one or more halogen atoms; Y is halogen, CF₃ orphenyl optionallysubstituted with one or morehalogen atoms, NO₂ groups, CN groups, C₁ -C₄alkyl groups optionally substituted with one or more halogen atoms, orC₁ -C₄ alkoxy groups optionally substituted with one or more halogenatoms; Z is hydrogen, halogen or CF₃ ; R is hydrogen or C₁ -C₄ alkyl; R₁and R₂ are each independently hydrogen,C₁ -C₆ alkyl optionallysubstituted with one or more halogen atoms, C₁ -C₆ alkoxy optionallysubstituted with one or more halogen atoms, C₁ -C₆ alkylthio optionallysubstituted with one or more halogen atoms, or phenyl optionallysubstituted with one ormore halogen atoms, NO₂ groups, CN groups, C₁ -C₄alkyl groups optionally substituted with one or more halogen atoms, orC₁ -C₄ alkoxy groups optionally substituted with one or more halogenatoms, or when R₁ and R₂ are taken together with the atom to which theyare attached may form a C₃ -C₆ cycloalkyl group optionally substitutedwith one to three C₁ -C₄ alkyl groups, C₂ -C₆ alkenyl groups or phenylgroups, or R₁ or R₂ may be taken together with R₃ and the atoms to whichthey are attached to form a 4- to 7-membered heterocyclic ring; Q is AR₃or ##STR41## A is O or S(O)_(p) ; p is an integer of 0, 1 or 2; R₃ ishydrogen,C₁ -C₆ alkyl, C₂ -C₆ alkenyl, C₂ -C₆ alkynyl, phenyl optionallysubstituted with one or morehalogen atoms, NO₂ groups, CN groups, C₁ -C₄alkyl groups optionally substituted with one or more halogen atoms, orC₁ -C₄ alkoxy groups optionally substituted with one or more halogenatoms, C(O)R₇ provided p is 0, C(O)A₁ provided p is 0, (CH₂ CH₂ O)_(n)R₇, or ##STR42## or R₃ may be taken together with either R₁ or R₂ andthe atoms to which they are attached to form a 4- to 7-memberedheterocyclic ring; Z₁ is O or S; R₇ isC₁ -C₆ alkyl, C₂ -C₆ alkenyl, C₂-C₆ alkynyl, or phenyl optionally substituted with one or morehalogenatoms, NO₂ groups, CN groups, C₁ -C₄ alkyl groups optionally substitutedwith one or more halogen atoms, or C₁ -C₄ alkoxy groups optionallysubstituted with one or more halogen atoms; n is an integer of 1, 2 or3; R₈ and R₉ are each independently hydrogen or C₁ -C₄ alkyl, orwhentaken together may form a ring wherein R₈ R₉ is represented by--CH═CH--CH═CH--; A₁ is OR₁₀ or NR₁₁ R₁₂ ; R₁₀ is C₁ -C₆ alkyl orphenyloptionally substituted with one ormore halogen atoms, NO₂ groups, CNgroups, C₁ -C₄ alkyl groups optionally substituted with one or morehalogen atoms, or C₁ -C₄ alkoxy groups optionally substituted with oneor more halogen atoms; R₁₁ and R₁₂ are each independently hydrogen or C₁-C₄ alkyl; and R₁₃ is C₁ -C₄ alkyl.
 11. The compound according to claim10 whereinW is CN, NO₂, S(O)_(m) CF₂ R₄ or ##STR43## R₄ is hydrogen, F,Cl, Br, CF₂ H, CCl₂ H, CF₃ or CCl₃ ; m is an integer of 0, 1 or 2; R₅and R₆ are each independently hydrogen or C₁ -C₄ alkyl; X is Cl, Br, CF₃orphenyl optionally substituted with one or morehalogen atoms, NO₂groups, CN groups, C₁ -C₄ alkyl groups optionally substituted with oneor more halogen atoms, or C₁ -C₄ alkoxy groups optionally substitutedwith one or more halogen atoms; Y is Cl, Br, CF₃ orphenyl optionallysubstituted with one or morehalogen atoms, NO₂ groups, CN groups, C₁ -C₄alkyl groups optionally substituted with one or more halogen atoms, orC₁ -C₄ alkoxy groups optionally substituted with one or more halogenatoms; Z is Cl, Br or CF₃ ; R is hydrogen; R₁ and R₂ are eachindependently hydrogen,C₁ -C₆ alkyl optionally substituted with one ormore halogen atoms, or R₁ or R₂ are taken together with R₃ and the atomsto which they are attached to form a 5- to 6-membered heterocyclic ring;Q is AR₃ or ##STR44## A is O or S; R₃ is C₁ -C₆ alkyl,phenyl optionallysubstituted with one or morehalogen atoms, NO₂ groups, CN groups, C₁ -C₄alkyl groups optionally substituted with one or more halogen atoms, orC₁ -C₄ alkoxy groups optionally substituted with one or more halogenatoms; (CH₂ CH₂ O)_(n) R₇, or ##STR45## or R₃ may be taken together witheither R₁ or R₂ and the atoms to which they are attached to form a 5- to6-membered heterocyclic ring; Z₁ is O or S; R₇ is C₁ -C₆ alkyl, n is aninteger of 1, 2 or 3; R₈ and R₉ are each independently hydrogen or C₁-C₄ alkyl, orwhen taken together may form a ring wherein R₈ R₉ isrepresented by --CH═CH--CH═CH--; and R₁₃ is C₁ -C₄ alkyl.
 12. Thecompound according to claim 11 whereinW is CN; X is phenyl optionallysubstituted with one or morehalogen atoms, NO₂ groups, CN groups, C₁ -C₄alkyl groups optionally substituted with one or more halogen atoms, orC₁ -C₄ alkoxy groups optionally substituted with one or more halogenatoms; Y is Cl or Br; Z is Cl, Br or CF₃ ; R is hydrogen; R₁ and R₂ areeach independently hydrogen orC₁ -C₆ alkyl, or R₁ or R₂ are takentogether with R₃ and the atoms to which they are attached to form a5-membered heterocyclic ring; Q is AR₃ or ##STR46## A is O or S; R₃ isC₁ -C₆ alkyl,phenyl optionally substituted with one or morehalogenatoms, NO₂ groups, CN groups, C₁ -C₄ alkyl groups optionally substitutedwith one or more halogen atoms, or C₁ -C₄ alkoxy groups optionallysubstituted with one or more halogen atoms, (CH₂ CH₂ O)_(n) R₇, or##STR47## or R₃ may be taken together with either R₁ or R₂ and the atomsto which they are attached to form a 5-membered heterocyclic ring; Z₁ isO or S; R₇ is C₁ -C₆ alkyl, n is an integer of 1, 2 or 3; and R₁₃ is C₁-C₄ alkyl.
 13. The method according to claim 12 wherein the compound hasthe structural formula ##STR48##
 14. The method according to claim 13wherein the compound is selected from the group consisting of[3-bromo-5-(p-chlorophenyl)-4-cyano-2-(trifluoromethyl)pyrrol-1-yl]methylmethyl carbonate;[3-bromo-5-(p-chlorophenyl)-4-cyano-2-(trifluoromethyl)pyrrol-1-yl]methyl2-furoate;[4-bromo-2-(p-chlorophenyl)-3-cyano-5-(trifluoromethyl)pyrrol-1-yl]methylphenoxyacetate;[3-bromo-5-(p-chlorophenyl)-4-cyano-2-(trifluoromethyl)pyrrol-1-yl]methyl(p-chlorophenoxy)acetate;[3-bromo-5-(p-chlorophenyl)-4-cyano-2-(trifluoromethyl)pyrrol-1-yl]methyl(phenylthio)acetate;[3-bromo-5-(p-chlorophenyl)-4-cyano-2-(trifluoromethyl)pyrrol-1-yl]methyl2-phenoxypropionate;[3-bromo-5-(p-chlorophenyl)-4-cyano-2-(trifluoromethyl)pyrrol-1-yl]methyl2-thiophenecarboxylate;[3-bromo-5-(p-chlorophenyl)-4-cyano-2-(trifluoromethyl)pyrrol-1-yl]methyl{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}acetate;[3,4-dichloro-4-cyano-5-(alpha,alpha,alpha-trifluoromethyl-p-tolyl)pyrrol-1-yl]methyl2-furoate;[3-bromo-5-(p-chlorophenyl)-4-cyano-2-(trifluoromethyl)pyrrol-1-yl]methyltetrahydro-2-furoate; and[3-chloro-5-(p-chlorophenyl)-4-cyano-2-(trifluoromethyl)pyrrol-1-yl]methyl(dimethylphosphono)acetate.
 15. A method for protecting growing plantsfrom attack by insects, acarina and mollusks which comprises applying tothe foliage of said plants or to the soil or water in which they aregrowing an insecticidally, acaricidally or molluscicidally effectiveamount of a compound having the structural formula ##STR49## wherein W,X, Y, Z, R, R₁, R₂ and Q are as described in claim
 10. 16. The methodaccording to claim 15 whereinW is CN, NO₂, S(O)_(m) CF₂ R₄ or ##STR50##R₄ is hydrogen, F, Cl, Br, CF₂ H, CCl₂ H, CF₃ or CCl₃ ; m is an integerof 0, 1 or 2; R₅ and R₆ are each independently hydrogen or C₁ -C₄ alkyl;X is Cl, Br, CF₃ orphenyl optionally substituted with one or morehalogenatoms, NO₂ groups, CN groups, C₁ -C₄ alkyl groups optionally substitutedwith one or more halogen atoms, or C₁ -C₄ alkoxy groups optionallysubstituted with one or more halogen atoms; Y is Cl, Br, CF₃ orphenyloptionally substituted with one or morehalogen atoms, NO₂ groups, CNgroups, C₁ -C₄ alkyl groups optionally substituted with one or morehalogen atoms, or C₁ -C₄ alkoxy groups optionally substituted with oneor more halogen atoms; Z is Cl, Br or CF₃ ; R is hydrogen; R₁ and R₂ areeach independently hydrogen,C₁ -C₆ alkyl optionally substituted with oneor more halogen atoms, or R₁ or R₂ are taken together with R₃ and theatoms to which they are attached to form a 5- to 6-membered heterocyclicring; Q is AR₃ or ##STR51## A is O or S; R₃ is C₁ -C₆ alkyl,phenyloptionally substituted with one or morehalogen atoms, NO₂ groups, CNgroups, C₁ -C₄ alkyl groups optionally substituted with one or morehalogen atoms, or C₁ -C₄ alkoxy groups optionally substituted with oneor more halogen atoms; (CH₂ CH₂ O)_(n) R₇, or ##STR52## or R₃ may betaken together with either R₁ or R₂ and the atoms to which they areattached to form a 5- to 6-membered heterocyclic ring; Z₁ is O or S; R₇is C₁ -C₆ alkyl, n is an integer of 1, 2 or 3; R₈ and R₉ are eachindependently hydrogen or C₁ -C₄ alkyl, orwhen taken together may form aring wherein R₈ R₉ is represented by --CH═CH--CH═CH--; and R₁₃ is C₁ -C₄alkyl.
 17. The compound according to claim 16 whereinW is CN; X isphenyl optionally substituted with one or morehalogen atoms, NO₂ groups,CN groups, C₁ -C₄ alkyl groups optionally substituted with one or morehalogen atoms, or C₁ -C₄ alkoxy groups optionally substituted with oneor more halogen atoms; Y is Cl or Br; Z is Cl, Br or CF₃ ; R ishydrogen; R₁ and R₂ are each independently hydrogen orC₁ -C₆ alkyl, orR₁ or R₂ are taken together with R₃ and the atoms to which they areattached to form a 5-membered heterocyclic ring; Q is AR₃ or ##STR53## Ais O or S; R₃ is C₁ -C₆ alkyl,phenyl optionally substituted with one ormorehalogen atoms, NO₂ groups, CN groups, C₁ -C₄ alkyl groups optionallysubstituted with one or more halogen atoms, or C₁ -C₄ alkoxy groupsoptionally substituted with one or more halogen atoms, (CH₂ CH₂ O)_(n)R₇, or ##STR54## or R₃ may be taken together with either R₁ or R₂ andthe atoms to which they are attached to form a 5-membered heterocyclicring; Z₁ is O or S; R₇ is C₁ -C₆ alkyl, n is an integer of 1, 2 or 3;and R₁₃ is C₁ -C₄ alkyl.
 18. The method according to claim 17 whereinthe compound has the structural formula ##STR55##
 19. The methodaccording to claim 18 wherein the compound is selected from the groupconsisting of[3-bromo-5-(p-chlorophenyl)-4-cyano-2-(trifluoromethyl)pyrrol-1-yl]methylmethyl carbonate;[3-bromo-5-(p-chlorophenyl)-4-cyano-2-(trifluoromethyl)pyrrol-1-yl]methyl2-furoate;[4-bromo-2-(p-chlorophenyl)-3-cyano-5-(trifluoromethyl)pyrrol-1-yl]methylphenoxyacetate;[3-bromo-5-(p-chlorophenyl)-4-cyano-2-(trifluoromethyl)pyrrol-1-yl]methyl(p-chlorophenoxy)acetate;[3-bromo-5-(p-chlorophenyl)-4-cyano-2-(trifluoromethyl)pyrrol-1-yl]methyl(phenylthio)acetate;[3-bromo-5-(p-chlorophenyl)-4-cyano-2-(trifluoromethyl)pyrrol-1-yl]methyl2-phenoxypropionate;[3-bromo-5-(p-chlorophenyl)-4-cyano-2-(trifluoromethyl)pyrrol-1-yl]methyl2-thiophenecarboxylate;[3-bromo-5-(p-chlorophenyl)-4-cyano-2-(trifluoromethyl)pyrrol-1-yl]methyl{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}acetate;[3,4-dichloro-4-cyano-5-(alpha,alpha,alpha-trifluoromethyl-p-tolyl)pyrrol-1-yl]methyl2-furoate;[3-bromo-5-(p-chlorophenyl)-4-cyano-2-(trifluoromethyl)pyrrol-1-yl]methyltetrahydro-2-furoate; and[3-chloro-5-(p-chlorophenyl)-4-cyano-2-(trifluoromethyl)pyrrol-1-yl]methyl(dimethylphosphono)acetate.
 20. The method according to claim 15 whereinthe compound is applied to the plants or soil in which they are growingat a rate of about 0.100 kg/ha to 4.0 kg/ha.
 21. A composition forcontrolling insects, acarina and mollusks comprising an agronomicallyacceptable carrier and an insecticidally, acaricidally ormolluscicidally effective amount of a compound having the structuralformula ##STR56## wherein W, X, Y, Z, R, R₁, R₂ and Q are as describedin claim
 10. 22. The composition according to claim 21 whereinW is CN,NO₂, S(O)_(m) CF₂ R₄ or ##STR57## R₄ is hydrogen, F, Cl, Br, CF₂ H, CCl₂H, CF₃ or CCl₃ ; m is an integer of 0, 1 or 2; R₅ and R₆ are eachindependently hydrogen or C₁ -C₄ alkyl; X is Cl, Br, CF₃ orphenyloptionally substituted with one or morehalogen atoms, NO₂ groups, CNgroups, C₁ -C₄ alkyl groups optionally substituted with one or morehalogen atoms, or C₁ -C₄ alkoxy groups optionally substituted with oneor more halogen atoms; Y is Cl, Br, CF₃ orphenyl optionally substitutedwith one or morehalogen atoms, NO₂ groups, CN groups, C₁ -C₄ alkylgroups optionally substituted with one or more halogen atoms, or C₁ -C₄alkoxy groups optionally substituted with one or more halogen atoms; Zis Cl, Br or CF₃ ; R is hydrogen; R₁ and R₂ are each independentlyhydrogen,C₁ -C₆ alkyl optionally substituted with one or more halogenatoms, or R₁ or R₂ are taken together with R₃ and the atoms to whichthey are attached to form a 5- to 6-membered heterocyclic ring; Q is AR₃or ##STR58## A is O or S; R₃ is C₁ -C₆ alkyl,phenyl optionallysubstituted with one or morehalogen atoms, NO₂ groups, CN groups, C₁ -C₄alkyl groups optionally substituted with one or more halogen atoms, orC₁ -C₄ alkoxy groups optionally substituted with one or more halogenatoms; (CH₂ CH₂ O)_(n) R₇, or ##STR59## or R₃ may be taken together witheither R₁ or R₂ and the atoms to which they are attached to form a 5- to6-membered heterocyclic ring; Z₁ is O or S; R₇ is C₁ -C₆ alkyl, n is aninteger of 1, 2 or 3; R₈ and R₉ are each independently hydrogen or C₁-C₄ alkyl, orwhen taken together may form a ring wherein R₈ R₉ isrepresented by --CH═CH--CH═CH--; and R₁₃ is C₁ -C₄ alkyl.
 23. Thecompound according to claim 22 whereinW is CN; X is phenyl optionallysubstituted with one or morehalogen atoms, NO₂ groups, CN groups, C₁ -C₄alkyl groups optionally substituted with one or more halogen atoms, orC₁ -C₄ alkoxy groups optionally substituted with one or more halogenatoms; Y is Cl or Br; Z is Cl, Br or CF₃ ; R is hydrogen; R₁ and R₂ areeach independently hydrogen orC₁ -C₆ alkyl, or R₁ or R₂ are takentogether with R₃ and the atoms to which they are attached to form a5-membered heterocyclic ring; Q is AR₃ or ##STR60## A is O or S; R₃ isC₁ -C₆ alkyl,phenyl optionally substituted with one or morehalogenatoms, NO₂ groups, CN groups, C₁ -C₄ alkyl groups optionally substitutedwith one or more halogen atoms, or C₁ -C₄ alkoxy groups optionallysubstituted with one or more halogen atoms, (CH₂ CH₂ O)_(n) R₇, or##STR61## or R₃ may be taken together with either R₁ or R₂ and the atomsto which they are attached to form a 5-membered heterocyclic ring; Z₁ isO or S; R₇ is C₁ -C₆ alkyl, n is an integer of 1, 2 or 3; and R₁₃ is C₁-C₄ alkyl.